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Inhibitors of sterol biosynthesis. Carbon-13 nuclear magnetic resonance studies of 9 alpha-fluoro-5 alpha-cholest-8(14)-en-3 beta-ol-15-one and related compounds. 1981

M Tsuda, and G J Schroepfer

The natural abundance 13C nuclear magnetic resonance spectra of a number of 9 alpha-fluoro and 9 alpha-hydroxy-delta 8(14)-15-ketosterols and their derivatives have been studied. Peak assignments for individual carbons of 9 alpha-fluoro-5 alpha-cholest-8(14)-en-3 beta-ol-15-one, 9 alpha-hydroxy-5 alpha-cholest-8(14)-en-3 beta-ol-15-one, 5 alpha-cholest-8(14)-ene-3,15-dione, 9 alpha-fluoro-5 alpha-cholest-8(14)-ene-3,15-dione, 9 alpha-hydroxy-5 alpha-cholest-8(14)-ene-3,15-dione, 3 beta-benzoyloxy-5 alpha-cholest-8(14)-en-3 beta-ol-15-one, 3 beta-benzoyloxy-9 alpha-fluoro-5 alpha-cholest-8(14)-en-15-one, 3 beta-benzoyloxy-5 alpha-cholest-8(14)-en-9 alpha-ol-15-one, 3 beta-acetoxy-9 alpha-fluoro-5 alpha-cholest-8(14)-en-15-one, and 3 beta-acetoxy-5 alpha-cholest-8(14)-en-9 alpha-ol-15-one have been made. Also presented herein are: 1) considerations of the substituent effects of the 9 alpha-hydroxy and 9 alpha-fluoro groups on carbon shieldings, 2) demonstration that the state of oxidation of C-3 in the various delta 8(14)-15-ketosteroids affects the olefinic carbon shieldings due to an apparent long range through space effect of the electric field on the olefinic carbon shieldings, 3) the results of analyses of 13C-19F spin-spin couplings, and 4) the results of considerations of 13C nuclear magnetic resonance studies of the concerned compounds with respect to the conformation of ring B in the various 9 alpha-substituted sterols.

UI MeSH Term Description Entries
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D002782 Cholestenes Steroids with methyl groups at C-10 and C-13 and a branched 8-carbon chain at C-17. Members include compounds with any degree of unsaturation; however, CHOLESTADIENES is available for derivatives containing two double bonds.
D002783 Cholestenones CHOLESTENES with one or more double bonds and substituted by any number of keto groups.
D013261 Sterols Steroids with a hydroxyl group at C-3 and most of the skeleton of cholestane. Additional carbon atoms may be present in the side chain. (IUPAC Steroid Nomenclature, 1987) Sterol
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships

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